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Since the days of Wild Style and Krush Groove, rappers have put their music on hold and delved into the film world. A bunch of these efforts were pretty bad—remember Ice-T in Leprechaun in the Hood—while others were so bad they were good. Cam crying in Killa Season or KRS fleeing the scene without a word in Who’s The Man? had some unintentional comedy, as did DMX trying to explain to Nas what our purpose on earth is (“Shorty can’t eat no books!”) in Belly. And then there were the ones that were actually straight-up good.
The 18 films that follow didn’t get much in the way of Oscar recognition, but if cinema is meant to entertain, well, they do that and then some.
Though the acting is cringe-inducing, it’s still shot beautifully by Hype Williams. Film buffs say it’s one long music video, and it kind of is. But it still looks great. Personally I watch it at least once a month, and a lot of rappers still make reference to it.
2. Paper Soldiers
Kevin Hart stars alongside Beanie Sigel, N.O.R.E., and a few others as a bumbling house burglar who means well but can’t seem to get anything right. The highlight is definitely when Beans puts the beats on an overzealous cop. Charlie Murphy wrote the screenplay so… yeah.
3. State Property 2
The sequel made the cut just off of sheer humor. The subject matter was the same as the first movie, but the writers and actors didn’t take themselves too seriously, making for more believable characters. N.O.R.E. really did his thing in this, as did Oschino Sparks. What the fidididduck?
HBO released this 1993 movie about gunrunners in Brooklyn. Though Bokeem Woodbine was the lead, Fredro Starr played the grimy Bamboo. Dude pulled a gun over a sandwich (he was getting screwed, though) and later even shot at Bokeem in his mom’s living room with the whole family there! Yeeesh. Das EFX and a slew of other rappers make cameos.
5. Paid In Full
Number 5 should be Number 1 to me. Based on Rich Porter, Alpo Martinez and Azie Faison—the Harlem trio that made millions a week in the 1980s—this film probably ranked highest as far as acting. Cam’ron embodied the Harlem hustler persona, playing the brash, cold-blooded Rico with Wood Harris on the opposite end of the spectrum playing Ace, the quiet, fair mastermind of the multimillion Harlem drug ring. Mekhi Phifer was decent as Money Mitch, but my favorite was N.O.R.E.’s little contribution. Don’t blink or you’ll miss it.
6. Who’s The Man?
Straight comedy. Ed Lover and Dr. Dre become cops (much to Dennis Leary’s dismay) to do their best Scooby Doo and Shaggy impressions and solve the murder of their boss and a pillar of their Harlem community. Even House of Pain was in this joint.
7. Killa Season
Director Cameron Giles (“I made it, Ma!”) puts together a hodgepodge storyline about selling drugs when hoop dreams deflate. Horrendous acting but still it’s somehow entertaining. But the scene with the drug mule “delivering” the drugs at the connect’s spot? No words for that. Damn, Killa you’re a sick son of a bitch.
Of course Pac was riveting as Bishop, but the real acting came from the bar/robbery scene. When Blizzard pulls the pump out, EPMD shine in their brief cameo. Erick and Parish’s facial expressions are worth the price of admission alone, Oscar worthy acting to say the least.
9. I’m ‘Bout It
The bum with the kitchen glass begging for beer is the funniest thing here, unless you count the run-up within three-feet-of-you-shootouts and rescue missions. This was low budget as shit, but it was still the first of the DIY genre of rapper movies.
10. Brooklyn Babylon
Don’t laugh. It was like our generation’s West Side Story, only in Crown Heights with Jews and Black citizens fighting instead of Irish and Puerto Rican gangs. OK, you can laugh now.
Ice Cube and Ice-T in one movie? So Icey. This is like Pacino and DeNiro. Not really. It fact it was pretty far from it actually. This one is all about buried treasure if you can believe it. And the hobo walks away with all the fig newtons. Go figure. Corny dialogue will have you chuckling all through out.
12. Cool As Ice
13. House Party
This movie has it all—bullies, broads, lessons in safe sex, cop chases, Robin Harris and Full Force. It worked so well, Kid N’ Play became a Saturday morning cartoon and dropped two more House Party movies. I don’t remember HP3 that well, but HP2 was hilarious with the pajama jammy jam.
The Fat Boys, Markie, Buffy and Kool are hired as orderlies to help inadvertently croak an old rich guy so his nephew can use the inheritance to pay off gambling debts. Pretty funny except for the racist cops.
15. How High
Number 15 should be Number 1 to me. Wait… Did I already make that Biggie reference earlier? Oh. Totally forgot. See this movie came on while I was hard at work composing this list, and, well… yeah. Wait… what were we talking about again?
16. Black and White
It should’ve been called Black and Yellow#&0151;pretty much the entire Clan is in it, with Oli “Power” Grant and Raekwon in the lead. It’s about rich prep school kids adopting black culture as their own and vice versa. (Well, not much vice versa, honestly.) Frodo Baggins gets his girl taken, and Allan Houston gets murked. And of course the best moment in cinematic history… Mike Tyson smacking Robert Downey, Jr. repeatedly, with a little choke thrown in for good measure.
17. Coffee and Cigarettes
I know I know… just one of five vignettes has anything to do with rappers. However, if that one vignette features GZA talking with Bill “Groundhog-Day-Ghostbustin’-Ass” Murray then that’s all that’s needed to make this list. Bill even calls RZA Bobby Digital. That’s like… bong, bong.
18. Ghost Dog: The Way Of The Samurai
This shouldn’t really be on the list; the rapper presence is not really that strong, at least not physically. (RZA composed the score.) It gets my vote off the strength of Ray Vargo (Henry Silva) rapping Flavor Flav lyrics verbatim. Then Handsome Frank (Richard Portnow) chimes in about Indian names. If that’s not the best ode to rap, I don’t know what is.